Abstract
Photochemical reactions of acyl iodides RC(O)I (R = Me, Ph) with aryl halides, fluoro-, chloro-, and bromobenzenes, 1,4-dibromobenzene, 2- and 3-bromotoluenes, and 4-bromo-1,2-dimethylbenzene, were studied. Acetyl iodide reacted with chloro- and bromobenzenes and 1,4-dibromobenzene according to the exchange pattern to give iodobenzene and 1,4-diiodobenzene, respectively. No halogen exchange was observed in the reactions of acetyl iodide with fluorobenzene and hexafluorobenzene. Benzoyl iodide failed to react with chloro- and brombenzene under UV irradiation but underwent polycondensation with formation of black nonfusible oligomers which were found to possess paramagnetic and semiconducting properties. Ultraviolet irradiation of a mixture of MeCOI with 2- or 3-bromotoluene, as well as with 4-bromo-1,2-dimethylbenzene, also led to the formation of polymeric products as a result of polycondensation of aryl iodides formed initially via replacement of bromine by iodine. Irradiation of benzoyl iodide in 2- or 3-bromotoluene involved recombination of benzoyl radicals to give benzil as the only product.
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Dedicated to Full Member of the Russian Academy of Sciences G.A. Tolstikov on his 80th anniversary
Original Russian Text © M.G. Voronkov, N.N. Vlasova, L.I. Belousova, A.V. Vlasov, T.I. Vakul’skaya, G.F. Prozorova, S.S. Khutsishvili, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 1, pp. 27–31.
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Voronkov, M.G., Vlasova, N.N., Belousova, L.I. et al. Photochemical reactions of acyl iodides with aryl halides. Russ J Org Chem 49, 17–21 (2013). https://doi.org/10.1134/S1070428013010041
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DOI: https://doi.org/10.1134/S1070428013010041